Multiple Cycloadditive Macrocyclization: An Efficient Method for Crown Ether-Type Cyclophanes, Bis-Calix[4]arenes and Silamacrocycles

Abstract

Macrocycles constitute a broad spectrum of compounds, which play a significant role in host-guest supramolecular chemistry. We have rationally designed an efficient novel synthetic method to synthesize different types of artificial receptive macrocycles containing isoxazoline or isoxazole ring systems. This method involves multiple (double, triple or quadruple) cycloadditions between bifunctional dipoles and bifunctional dipolarophiles. We have presented our synthetic results to show the ease with which this one-pot synthetic method can be extended to synthesize different types of macrocycles such as cyclophanes, bis-calix[4]arenes and silamacrocycles. Hence, with appropriate combination of bifunctional dipoles and bifunctional dipolarophiles, the ring size of macrocycles could be controlled. This multiple cycloadditive macrocyclization will be a useful arsenal for the synthesis of various macrocycles.

Key words

cycloadditions - cyclophanes - macrocycles - nitrile oxides - silicon heterocycles

References

• 1a In Advances in Cycloaddition   Vol 4:  Curran DP. Jai press; London: 1997. 
• 1b Kim BH. Synth. Commun.  1987,  17:  1199 
• 1c Kim BH. Progress in Chemistry and Chemical Industry  1991,  31:  242 
• 1d Kim BH. Lee JY. Kim K. Whang D. Tetrahedron: Asymmetry  1991,  2:  27 
• 1e Kim BH. Lee JY. Tetrahedron: Asymmetry  1991,  2:  1359 
• 1f Keum G. Chung YJ. Kim BH. Bull. Korean Chem. Soc.  1992,  13:  343 
• 1g Kim BH. Lee JY. Tetrahedron Lett.  1992,  33:  2557 
• 1h Kim BH. Chung YJ. Keum G. Kim J. Kim K. Tetrahedron Lett.  1992,  33:  6811 
• 1i Kim BH. Curran DP. Tetrahedron  1993,  49:  293 
• 1j Kim KS. Kim BH. Park WM. Cho SJ. Mhin BJ. J. Am. Chem. Soc.  1993,  115:  7472 
• 1k Lee JY. Kim BH. Tetrahedron Lett.  1995,  36:  3361 
• 1l Lee JY. Kim BH. Tetrahedron  1996,  52:  571 
• 1m Kim SJ. Lee JY. Kim BH. Bioorg. Med. Chem. Lett.  1998,  8:  1313 
• 2a In Macrocyclic Synthesis: A practical Approach   Parker D. Oxford University Press; Oxford: 1996. 
• 2b Inone Y. Gokel GW. In Cation Binding by Macrocycles: Complexation of Cationic Species by Crown Ethers   Marcel Dekker; New York: 1990. 
• 3 Dietrich B. Viout P. Lehn J.-M. In Macrocyclic Chemistry   VCH; Weinheim: 1993. 
• 4 Kim BH. Jeong EJ. Jung WH. J. Am. Chem. Soc.  1995,  11:  6390 
• 5a Garanti L. Sala A. Zecchi G. J. Org. Chem.  1975,  40:  2403 
• 5b Heinz I. Knoll K. Muller R. Eberbach W. Chem. Ber.  1989,  122:  2147 ; and references cited therein
• 6 Broggni G. Garanti L. Molteni G. Zecchi G. Tetrahedron  1998,  54:  2843 ; and the references recited therein
• 7 Asaoka M. Mukuta T. Takei H. Tetrahedron Lett.  1981,  22:  735 
• 8 Engelbach M. Imming P. Seitz G. Tegethoff R. Heterocycles  1995,  40:  69 
• 9 Mass G. Gettwert V. Krebs F. Schmidtberg G. Chem.- Eur. J.  2000,  6:  1646 
• 10 Nishimura J. Nakamura Y. Hayashida Y. Kudo T. Acc. Chem. Res.  2000,  33:  679 
• 11a Nishimura J. Nakamura Y. Hayashida Y. Kudo T. Synlett  1994,  884 
• 11b Okada Y. Nishimura J. J. Inclusion Phenom.  1994,  19:  41 
• 12 Sato M. Uehara F. Sato K. Yamaguchi M. Kabuto C. J. Am. Chem. Soc.  1999,  121:  8270 
• 13a Callot HL. Johnson AW. Sweeney A. J. Chem. Soc., Perkin Trans. 1  1973,  1424 
• 13b Mettath S. Dougherty TJ. Pandey RK. Tetrahedron Lett.  1999,  40:  6171 
• 13c Sheng G. Shibata M. Dougherty TJ. Pandey RK. J. Org. Chem.  2000,  65:  543 
• 14a Girrester U. Giuffrida D. Kohnke FH. Mathias JP. Philip D. Stoddart JF. Pure Appl. Chem.  1993,  65:  119 
• 14b Kohnke FH. Slawin AMZ. Stoddart JF. Williams DJ. Angew. Chem., Int. Ed. Engl.  1987,  29:  892 
• 14c Stoddart JF. J. Inclusion Phenom.  1989,  7:  227 
• 15 Godt A. Enkelmann V. Schluter A.-D. Angew. Chem., Int. Ed. Engl.  1989,  28:  1680 
• 16 Cory RM. McPhill CL. Dikmans AJ. Vital JJ. Tetrahedron Lett.  1996,  37:  1983 
• 17 Huisgen R. Angew. Chem., Int. Ed. Engl.  1963,  2:  565 
• 18a Gutsche CD. Top. Curr. Chem.  1984,  123:  1 
• 18b Gutsche CD. In Calixarenes: Monographs in Supramolecular Chemistry   Vol. 1:  Stoddart JF. The Royal Society of Chemistry; Cambridge: 1989. 
• 18c Gutsche CD. In Calixarenes Revisited: Monographs in Supramolecular Chemistry   Stoddart JF. The Royal Society of Chemistry; Cambridge: 1998. 
• 19 Rudkevich DM. Verboom W. Reinhoudt DN. J. Org. Chem.  1994,  59:  3683 
• 20 Lee CW. Hwang GT. Kim BH. Tetrahedron Lett.  2000,  41:  4177 
• 21 Hwang GT. Kim BH. Tetrahedron Lett.  2000,  41:  10055 
• 22 Iwakura Y. Akiyama M. Nagakubo K. Bull. Chem. Soc. Jpn.  1964,  37:  767 
• 23 Maugein N. Wagner A. Mioskowski C. J. Org. Chem.  1999,  64:  8428 
• 24a König B. Rödel M. Bubenitschek P. Jones PG. Angew. Chem., Int. Ed. Engl.  1995,  34:  661 
• 24b Kauffmann T. Kniese H.-H. Tetrahedron Lett.  1973,  41:  4043 
• 24c Birkofer L. Stuhl O. J. Organomet. Chem.  1979,  177:  C16 
• 24d Kaes C. Hosseini MW. Ruppert R. De Cian A. Fischer J. Tetrahedron Lett.  1994,  35:  7233 
• 24e Kaes C. Hosseini MW. De Cian A. Fischer J. . Chem. Commun.  1997,  2229 
• 24f Jung ME. Xia H. Tetrahedron Lett.  1988,  29:  297 
• 25a Curran DP. J. Am. Chem. Soc.  1983,  105:  5826 
• 25b Kim BH. Chung YJ. Ryu EJ. Tetrahedron Lett.  1993,  34:  8465 
• 25c Kim BH. Ryu EJ. Chung YJ. Bioorg. Med. Chem. Lett.  1994,  4:  2799 
• 25d Kim DH. Choi KY. Chung YJ. Kim BH. J. Appl. Pharm.  1994,  2:  155 
• 25e Chung YJ. Ryu EJ. Keum G. Kim BH. Bioorg. Med. Chem.  1996,  4:  209